Aromatic amine derivative and organic electroluminescent element using same

ABSTRACT

An aromatic amine derivative represented by the following formula (1): 
                         
wherein at least one of R 1  to R 8  is a group other than a hydrogen atom, Ar 1  to Ar 4  are a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.

TECHNICAL FIELD

The invention relates to an organic electroluminescence device using anaromatic amine derivative and an anthracene derivative, and inparticular, to an organic electroluminescence device having a highchromatic purity and a long life, and an aromatic amine derivativerealizing it.

BACKGROUND ART

An organic electroluminescence (EL) device using an organic substance isa promising solid-state emitting type inexpensive and large full-colordisplay device, and has been extensively developed. In general, anorganic EL device includes an emitting layer and a pair of opposingelectrodes holding the emitting layer therebetween. When an electricfield is applied between the electrodes, electrons are injected from thecathode and holes are injected from the anode. Emission is a phenomenonin which the electrons recombine with the holes in the emitting layer toproduce an excited state, and energy is emitted as light when theexcited state returns to the ground state.

The performance of an organic EL device has been gradually improved withimprovements in emitting materials for an organic EL device. Inparticular, improvement in color purity (shortening of emissionwavelength) of a blue-emitting organic EL device is an important factorleading to high color reproducibility of a display.

As examples of a material for an emitting layer, Patent Documents 1 to 8disclose diaminopyrene derivatives. Patent Documents 3 to 8 discloseorganic EL devices using a diaminopyrene derivative as a dopingmaterial. Indeed, by using the materials described in these documents,properties of the organic EL device can be improved. However, it isdifficult to obtain pure blue light emission, whereby it is not easy touse those materials as a material for a display. Patent Documents 1 and2 disclose diaminopyrene derivatives which can emit blue light having ashort wave length. However, there is a problem that the luminouslifetime of the organic EL devices obtained by using these materials isvery short.

-   Patent Document 1: Korean Patent Publication No. 10-2007-0115588-   Patent Document 2: Korean Patent Publication No. 10-2008-0079956-   Patent Document 3: WO2005/108348-   Patent Document 4: WO2004/018588-   Patent Document 5: WO2004/018587-   Patent Document 6: WO2009/102054-   Patent Document 7: WO2009/102026-   Patent Document 8: WO2009/107596

DISCLOSURE OF THE INVENTION

An object of the invention is to provide a material for an organic ELdevice which can emit blue light which is high in color purity and has along luminous lifetime.

According to the invention, the following organic electroluminescentdevice and the like are provided.

1. An aromatic amine derivative represented by the following formula(1):

wherein R₁ to R₈ are independently a hydrogen atom, a halogen atom, asubstituted or unsubstituted alkyl group having 1 to 20 carbon atoms, asubstituted or unsubstituted cycloalkyl group having 3 to 10 carbonatoms, a substituted or unsubstituted alkylsilyl group having 3 to 30carbon atoms, a substituted or unsubstituted arylsilyl group having 8 to30 carbon atoms that form a ring (hereinafter referred to as “ringcarbon atoms”), a substituted or unsubstituted alkoxy group having 1 to20 carbon atoms, a substituted or unsubstituted aralkyl group having 6to 20 ring carbon atoms, or a substituted or unsubstituted aryl grouphaving 6 to 10 ring carbon atoms,

at least one of R₁ to R₈ is a group other than a hydrogen atom, and

Ar₁ to Ar₄ are a substituted or unsubstituted aryl group having 6 to 30ring carbon atoms, at least one of Ar₁ to Ar₄ is an aryl groupsubstituted with one or more substituents selected from a cyano group, afluorine atom, a halogenated alkyl group, a nitro group and a carbonylgroup,

provided that, when at least one of Ar₁ to Ar₄ is a p-fluorophenylgroup, at least one of Ar₁ to Ar₄ which are not a p-fluorophenyl groupis an aryl group other than a p-fluorophenyl group which is substitutedwith one or more substituents selected from a cyano group, a fluorineatom, a halogenated alkyl group, a nitro group and a carbonyl group.

2. The aromatic amine derivative according to 1, which is represented bythe following formula (2):

wherein R₁ to R₈, Ar₂ and Ar₄ are the same as those in the formula (1),

R₁₁ to R₂₀ are independently a hydrogen atom, a substituted orunsubstituted alkyl group having 1 to 20 carbon atoms, a substituted orunsubstituted alkylsilyl group having 3 to 30 carbon atoms, asubstituted or unsubstituted arylsilyl group having 8 to 30 ring carbonatoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbonatoms, a substituted or unsubstituted aralkyl group having 6 to 20 ringcarbon atoms, or a substituted or unsubstituted aryl group having 6 to10 ring carbon atoms, a cyano group, a fluorine atom, a halogenatedalkyl group, a nitro group or a carbonyl group, and

at least one of R₁₁ to R₁₅ is a cyano group, a fluorine atom, ahalogenated alkyl group, a nitro group or a carbonyl group, and at leastone of R₁₆ to R₂₀ is a cyano group, a fluorine atom, a halogenated alkylgroup, a nitro group or a carbonyl group.

3. The aromatic amine derivative according to 2, wherein one of R₁₁ toR₁₅ is a cyano group, and the remaining R₁₁ to R₁₅ are hydrogen atoms,and

one of R₁₆ to R₂₀ is a cyano group, and the remaining R₁₆ to R₂₀ arehydrogen atoms.

4. The aromatic amine derivative according to 3, wherein R₁, R₃, R₄, R₅,R₇ and R₈ are hydrogen atoms.

5. The aromatic amine derivative according to 4, wherein R₂ and R₆ areindependently a substituted or unsubstituted alkyl group having 1 to 20carbon atoms, a substituted or unsubstituted cycloalkyl group having 3to 10 carbon atoms or a substituted or unsubstituted silyl group having3 to 30 carbon atoms.

6. The aromatic amine derivative according to any one of 1 to 5, whereinAr₁ to Ar₄ are a substituted or unsubstituted aryl group having 6 to 30ring carbon atoms, and at least one of Ar₁ to Ar₄ is an aryl grouphaving one or more cyano groups.

7. An organic luminescent medium comprising the aromatic aminederivative according to any one of 1 to 6.

8. The organic luminescent medium according to 7, which comprises thearomatic amine derivative as a doping material.

9. The organic luminescent medium according to 7 further comprising ananthracene derivative represented by the following formula (10):

wherein Ar¹¹ and Ar¹² are independently a substituted or unsubstitutedaryl group having 6 to 30 ring carbon atoms or a substituted orunsubstituted heterocyclic group having 5 to 30 atoms that form a ring(hereinafter referred to as “ring atoms”), and

R¹⁰¹ to R¹⁰⁸ are independently a hydrogen atom, a fluorine atom, asubstituted or unsubstituted alkyl group having 1 to 10 carbon atoms, asubstituted or unsubstituted cycloalkyl group having 3 to 10 carbonatoms, a substituted or unsubstituted alkylsilyl group having 3 to 30carbon atoms, a substituted or unsubstituted arylsilyl group having 8 to30 ring carbon atoms, a substituted or unsubstituted alkoxy group having1 to 20 carbon atoms, a substituted or unsubstituted aryloxy grouphaving 6 to 20 ring carbon atoms, a substituted or unsubstituted arylgroup having 6 to 30 ring carbon atoms, or a substituted orunsubstituted heterocyclic group having 5 to 30 ring atoms.

10. The organic luminescent medium according to 9, wherein in theformula (10), Ar¹¹ and Ar¹² are independently a substituted orunsubstituted fused aromatic ring group having 10 to 30 ring carbonatoms.

11. The organic luminescent medium according to 9, wherein in theformula (10), Ar¹¹ is a substituted or unsubstituted phenyl group, andAr¹² is a substituted or unsubstituted fused aromatic ring group having10 to 30 ring carbon atoms.

12. The organic luminescent medium according to 11, wherein theanthracene derivative is represented by the following formula (10-4);

wherein R¹⁰¹ to R¹⁰⁸ are the same as those in formula (10),

R¹¹¹ is a substituted or unsubstituted aryl group having 6 to 30 ringcarbon atoms, a substituted or unsubstituted heterocyclic group having 5to 30 ring atoms, a substituted or unsubstituted alkyl group having 1 to10 carbon atoms, a substituted or unsubstituted cycloalkyl group having3 to 10 ring carbon atoms, a substituted or unsubstituted alkoxy grouphaving 1 to 20 carbon atoms, a substituted or unsubstituted silyl group,a cyano group or a fluorine atom,

b is an integer of 0 to 7, and plural R¹¹¹s may be the same or differentwhen b is an integer of 2 or more, and

Ar⁶ is a substituted or unsubstituted aryl group having 6 to 30 ringcarbon atoms, a substituted or unsubstituted alkyl group having 1 to 10carbon atoms, a substituted or unsubstituted cycloalkyl group having 3to 10 ring carbon atoms or a substituted or unsubstituted heterocyclicgroup having 5 to 30 ring atoms, or Ar⁶ may form a ring with the benzenering to which Ar⁶ bonds.

13. The organic luminescent medium according to 11, wherein theanthracene derivative is represented by the following formula (10-5):

wherein R¹⁰¹ to R¹⁰⁸ are the same as those in formula (10),

R¹¹¹ is a substituted or unsubstituted aryl group having 6 to 30 ringcarbon atoms, a substituted or unsubstituted heterocyclic group having 5to 30 ring atoms, a substituted or unsubstituted alkyl group having 1 to10 carbon atoms, a substituted or unsubstituted cycloalkyl group having3 to 10 ring carbon atoms, a substituted or unsubstituted alkoxy grouphaving 1 to 20 carbon atoms, a substituted or unsubstituted silyl group,a cyano group or a fluorine atom,

b is an integer of 0 to 7, and plural R¹¹¹s may be the same or differentwhen b is an integer of 2 or more, and

Ar⁷ is a substituted or unsubstituted aryl group having 6 to 30 ringcarbon atoms, a substituted or unsubstituted alkyl group having 1 to 10carbon atoms, a substituted or unsubstituted cycloalkyl group having 3to 10 ring carbon atoms or a substituted or unsubstituted heterocyclicgroup having 5 to 30 ring atoms, or Ar⁷ may form a ring with the benzenering to which Ar⁷ bonds.

14. The organic luminescent medium according to 9, wherein theanthracene derivative is represented by the following formula (10-6):

wherein R¹⁰¹ to R¹⁰⁸ are the same as those in the formula (10),

Ar⁸ is a substituted or unsubstituted aryl group having 6 to 30 ringcarbon atoms, a substituted or unsubstituted alkyl group having 1 to 10carbon atoms, a substituted or unsubstituted cycloalkyl group having 3to 10 ring carbon atoms, or a substituted or unsubstituted heterocyclicgroup having 5 to 50 ring atoms, or Ar⁸ may form a ring with the benzenering to which Ar⁸ bonds, and

Ar⁹ is a substituted or unsubstituted aryl group having 6 to 30 ringcarbon atoms, a substituted or unsubstituted alkyl group having 1 to 10carbon atoms, a substituted or unsubstituted cycloalkyl group having 3to 10 ring carbon atoms, or a substituted or unsubstituted heterocyclicgroup having 5 to 50 ring atoms.

15. The organic luminescent medium according to 9, wherein theanthracene derivative is represented by the following formula (10-7):

wherein R¹⁰¹ to R¹⁰⁸ and Ar¹² are the same as those in the formula (10),

L is a single bond, a substituted or unsubstituted arylene group having6 to 30 ring carbon atoms or a substituted or unsubstituted divalentheterocyclic group having 5 to 30 ring atoms,

R¹²¹ is a substituted or unsubstituted aryl group having 6 to 30 ringcarbon atoms, a substituted or unsubstituted heterocyclic group having 5to 30 ring atoms, a substituted or unsubstituted alkyl group having 1 to10 carbon atoms, a substituted or unsubstituted cycloalkyl group having3 to 10 ring carbon atoms, a substituted or unsubstituted alkoxy grouphaving 1 to 20 carbon atoms, a substituted or unsubstituted silyl group,a cyano group or a fluorine atom, and

n is an integer of 0 to 11, and plural R¹²¹s may be the same ordifferent when n is an integer of 2 or more.

16. The organic luminescent medium according to 9, wherein theanthracene derivative is represented by the following formula (10-8):

wherein R¹⁰¹ to R¹⁰⁸ and Ar¹² are the same as those in the formula (10),

L is a single bond, a substituted or unsubstituted arylene group having6 to 50 ring carbon atoms or a substituted or unsubstituted divalentheterocyclic group having 5 to 50 ring atoms,

X¹¹ is an oxygen atom, a sulfur atom, or —NR— wherein R is the same asin R¹⁰¹ to R¹⁰⁸,

R¹²¹ is a substituted or unsubstituted aryl group having 6 to 30 ringcarbon atoms, a substituted or unsubstituted heterocyclic group having 5to 30 ring atoms, a substituted or unsubstituted alkyl group having 1 to10 carbon atoms, a substituted or unsubstituted cycloalkyl group having3 to 10 ring carbon atoms, a substituted or unsubstituted alkoxy grouphaving 1 to 20 carbon atoms, a substituted or unsubstituted silyl group,a cyano group or a fluorine atom, and

m is an integer of 0 to 7, and plural R¹²¹s may be the same or differentwhen m is an integer of 2 or more.

17. The organic luminescent medium according to 9, wherein theanthracene derivative is represented by the following formula (10-9):

wherein R¹⁰¹ to R¹⁰⁸ and Ar¹² are the same as those in the formula (10).

18. The organic luminescent medium according to 9, wherein theanthracene derivative is represented by the following formula (10-10):

wherein R¹⁰¹ to R¹⁰⁸ and Ar¹² are the same as those in the formula (10).

19. The organic luminescent medium according to 9, wherein in theformula (10), Ar¹¹ and Ar¹² are independently a group formed by 1 to 4hydrocarbon aromatic rings which may be substituted, and R¹⁰¹ to R¹⁰⁸are independently a hydrogen atom, an alkyl group having 1 to 4 carbonatoms, a silyl group or a silyl group substituted with an alkyl grouphaving 1 to 4 carbon atoms.

20. An organic electroluminescence device comprising a cathode, ananode, and one or more organic thin film layers comprising an emittinglayer therebetween,

wherein at least one layer of the organic thin film layers comprises thearomatic amine derivative according to any one of 1 to 6 singly or as acomponent of a mixture.

21. The organic electroluminescence device according to 20, wherein theemitting layer comprises the aromatic amine derivative.

According to the invention, an organic EL device which can emit bluelight which is high in color purity and has a long luminous lifetime canbe provided.

BEST MODE FOR CARRYING OUT THE INVENTION

The aromatic amine derivative of the invention is represented by thefollowing formula (1):

In the formula (1), R₁ to R₈ are independently a hydrogen atom, ahalogen atom, a substituted or unsubstituted alkyl group having 1 to 20carbon atoms, a substituted or unsubstituted cycloalkyl group having 3to 10 carbon atoms, a substituted or unsubstituted alkylsilyl grouphaving 3 to 30 carbon atoms, a substituted or unsubstituted arylsilylgroup having 8 to 30 ring carbon atoms, a substituted or unsubstitutedalkoxy group having 1 to 20 carbon atoms, a substituted or unsubstitutedaralkyl group having 6 to 20 ring carbon atoms, or a substituted orunsubstituted aryl group having 6 to 10 ring carbon atoms, at least oneof R₁ to R₈ is a group (including a halogen atom) other than a hydrogenatom, and

Ar₁ to Ar₄ are a substituted or unsubstituted aryl group having 6 to 30ring carbon atoms, at least one of Ar₁ to Ar₄ is an aryl group havingone or more groups or atoms selected from a cyano group, a fluorineatom, a halogenated alkyl group, a nitro group and a carbonyl group,

provided that, when at least one of Ar₁ to Ar₄ is a p-fluorophenylgroup, at least one of Ar₁ to Ar₄ which is not a p-fluorophenyl group isan aryl group other than a p-fluorophenyl group which is substitutedwith one or more substituents selected from a cyano group, a fluorineatom, a halogenated alkyl group, a nitro group and a carbonyl group.

The p-fluorophenyl group is a group in which a phenyl group issubstituted by a fluorine atom at the para position, and is notsubstituted by other substituents than this fluorine atom.

The aromatic amine derivative of the invention can have improvedluminous lifetime by allowing a predetermined substituent to be bondedto the pyrene ring. Further, since the aryl group of the diarylaminogroup has a cyano group, a fluorine atom, a halogenated alkyl group, anitro group or a carbonyl group, which are electron-attracting groups,blue emission which has a shorter emission wavelength as compared withconventional organic EL devices can be obtained. Hereinafter, a cyanogroup, a fluorine atom, a halogenated alkyl group, a nitro group or acarbonyl group may often be referred to as the “electron-attractinggroup”.

The electron-attracting group is a group having a function of decreasingthe electron density. Due to the presence of these electron-attractinggroups, excessive electrons are trapped and electrons are preventedelectrons from entering a hole-transporting material. As a result,deterioration of a hole-transporting material can be prevented, wherebyan organic EL device has a prolonged lifetime.

Preferable electron-attracting groups include a cyano group, a fluorineatom and a halogenated alkyl group, with a cyano group beingparticularly preferable.

Of the above-mentioned electron-attracting groups, it is considered thatthe fluorine atom has an effect of allowing an organic EL device to emitlight with a shorter wavelength due to the electronegativity thereof. Itis assumed that a shorter distance from the fluorine atom to N (i.e.distance to the main skeleton which affects the wavelength) can furtherimprove color purity.

Therefore, in respect of high color purity, in the formula (1), if atleast one of Ar₁ to Ar₄ is a p-fluorophenyl group, at least one ofremaining Ar₁ to Ar₄ is an aryl group which is substituted by one ormore groups or atoms other than the p-fluorophenyl group, i.e. one ormore groups or atoms selected from a cyano group, a fluorine atom, ahalogenated alkyl group, a nitro group and a carbonyl group.

The aromatic amine derivative of the invention is preferably representedby the following formula (2).

In the formula (2), R₁ to R₈ and Ar₂ and Ar₄ are the same as those inthe formula (1).

R₁₁ to R₂₀ are independently a hydrogen atom, a substituted orunsubstituted alkyl group having 1 to 20 carbon atoms, a substituted orunsubstituted alkylsilyl group having 3 to 30 carbon atoms, asubstituted or unsubstituted arylsilyl group having 8 to 30 ring carbonatoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbonatoms, a substituted or unsubstituted aralkyl group having 6 to 20 ringcarbon atoms, a substituted or unsubstituted aryl group having 6 to 10ring carbon atoms, a substituted or unsubstituted heterocyclic grouphaving 5 to 20 ring atoms, a cyano group, a fluorine atoms, ahalogenated alkyl group, a nitro group or a carbonyl group.

At least one of R₁₁ to R₁₅ is a cyano group, a fluorine atom, ahalogenated alkyl group, a nitro group or a carbonyl group and at leastone of R₁₆ to R₂₀ is a cyano group, a fluorine atom, a halogenated alkylgroup, a nitro group or a carbonyl group.

In respect of high color purity, in the formula (2), if R₁₃ or R₁₈ is anelectron-attracting group, it is preferred that R₁₃ or R₁₈ be one of acyano group, a halogenated alkyl group, a nitro group or a carbonylgroup. Further, it is preferred that R₁₃ and R₁₈ be one of a cyanogroup, a halogenated alkyl group, a nitro group or a carbonyl group, andthat the remaining are hydrogen atoms.

In the formula (2), it is preferred that one of R₁₁ to R₁₅ be a cyanogroup and the remaining be hydrogen atoms, and one of R₁₆ to R₂₀ be acyano group and the remaining be hydrogen atoms.

The aromatic amine derivative of the invention is preferably presentedby the following formula (3) or (4).

In the formula (3) or (4), R₁ to R₈ and Ar₂ and Ar₄ are the same asthose in the formula (1).

R₂₁ to R₄₈ are independently a hydrogen atom, a substituted orunsubstituted alkyl group having 1 to 20 carbon atoms, a substituted orunsubstituted alkylsilyl group having 3 to 30 carbon atoms, asubstituted or unsubstituted arylsilyl group having 8 to 30 ring carbonatoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbonatoms, a substituted or unsubstituted aralkyl group having 6 to 20 ringcarbon atoms, a substituted or unsubstituted aryl group having 6 to 10ring carbon atoms, a substituted or unsubstituted heterocyclic grouphaving 5 to 20 ring atoms, a cyano group, a fluorine atom, a halogenatedalkyl group, a nitro group or a carbonyl group.

It is preferred that at least one of R₂₁ to R₂₇ be a cyano group, afluorine atom, a halogenated alkyl group, a nitro group or a carbonylgroup and that at least one of R₂₈ to R₃₄ be a cyano group, a fluorineatom, a halogenated alkyl group, a nitro group or a carbonyl group.

In respect of high color purity, if at least one of R₂₂ to R₂₅ and/or atleast one of R₂₉ to R₃₂ is an electron-attracting group, it is preferredthat at least one of R₂₂ to R₂₅ and/or at least one of R₂₉ to R₃₂ be acyano group, a halogenated alkyl group, a nitro group or a carbonylgroup.

It is preferred that the remaining be hydrogen atoms.

Further, it is preferred that Ar₂ or Ar₄ be an aryl group which is otherthan a p-fluorophenyl group and is substituted by one or more selectedfrom a cyano group, a fluorine atom, a halogenated alkyl group, a nitrogroup and a carbonyl group, and that R₂₁ to R₃₄ be hydrogen atoms.

It is preferred that at least one of R₃₅ to R₄₁ be a cyano group, afluorine atom, a halogenated alkyl group, a nitro group or a carbonylgroup and at least one of R₄₂ to R₄₈ be a cyano group, a fluorine atom,a halogenated alkyl group, a nitro group or a carbonyl group.

In respect of high color purity, if at least one of R₃₅ to R₃₈ and/or atleast one of R₄₅ to R₄₈ is an electron-attracting group, it is preferredthat at least one of R₃₅ to R₃₈ and/or at least one of R₄₅ to R₄₈ be acyano group, a halogenated alkyl group, a nitro group or a carbonylgroup.

It is preferred that the remaining be hydrogen atoms.

Further, it is preferred that Ar₂ or Ar₄ be an aryl group which is otherthan a p-fluorophenyl group and is substituted by one or more selectedfrom a cyano group, a fluorine atom, a halogenated alkyl group, a nitrogroup and a carbonyl group, and that R₃₅ to R₄₈ be hydrogen atoms.

In addition, it is preferred that R₁, R₃, R₄, R₅, R₇ and R₈ be hydrogenatoms. Since R₂ and R₆ are the active sites of the pyrene ring, theactive sites can be protected by introducing a substituent to R₂ and R₆.As a result, the stability of the compound is improved.

It is particularly preferred that R₂ and R₆ be independently asubstituted or unsubstituted alkyl group having 1 to 20 carbon atoms, asubstituted or unsubstituted cycloalkyl group having 3 to 10 carbonatoms or a substituted or unsubstituted silyl group having 3 to 30carbon atoms. If R₂ and R₆ are these groups, the luminous life isparticularly improved.

In this specification, the “ring carbon” means a carbon atom whichconstitutes a saturated ring, an unsaturated ring or an aromatic ring.The “ring atom” means a carbon atom or a hetero atom which constitutes ahetero ring (including a saturated ring, an unsaturated ring and anaromatic ring).

Examples of substituents in “substituted or unsubstituted . . . ”include an alkyl group, alkylsilyl group, halogenated alkyl group, arylgroup, cycloalkyl group, alkoxy group, heterocyclic group, aralkylgroup, aryloxy group, arylthio group, alkoxycarbonyl group, halogenatom, hydroxyl group, nitro group, cyano group, carboxy group,dibenzofuranyl group and fluorenyl group as described below.

The hydrogen atom of the invention includes light hydrogen anddeuterium.

Specific examples of the groups in formulas (1) and (2), and thesubstituents are shown below.

Examples of the alkyl group include a methyl group, ethyl group, propylgroup, isopropyl group, n-butyl group, s-butyl group, isobutyl group,t-butyl group, n-pentyl group, n-hexyl group, n-heptyl group and n-octylgroup.

The alkyl group preferably has 1 to 10 carbon atoms, and more preferably1 to 6 carbon atoms. Of these, a methyl group, ethyl group, propylgroup, isopropyl group, n-butyl group, s-butyl group, isobutyl group,t-butyl group, n-pentyl group and n-hexyl group are preferable.

The alkylsilyl group is represented by —SiY₃, and examples of Y are thesame as those of the alkyl group.

As the aryl group, a phenyl group, 1-naphthyl group, 2-naphthyl group,1-anthryl group, 2-anthryl group, 9-anthryl group, 1-phenanthryl group,2-phenanthryl group, 3-phenanthryl group, 4-phenanthryl group,9-phenanthryl group, 1-naphthacenyl group, 2-naphthacenyl group,9-naphthacenyl group, 1-pyrenyl group, 2-pyrenyl group, 4-pyrenyl group,6-chrysenyl group, 1-benzo[c]phenanthryl group, 2-benzo[c]phenahthrylgroup, 3-benzo[c]phenanthryl group, 4-benzo[c]phenanthryl group,5-benzo[c]phenanthryl group, 6-benzo[c]phenanthryl group,1-benzo[g]chrysenyl group, 2-benzo[g]chrysenyl group,3-benzo[g]chrysenyl group, 4-benzo[g]chrysenyl group,5-benzo[g]chrysenyl group, 6-benzo[g]chrysenyl group,7-benzo[g]chrysenyl group, 8-benzo[g]chrysenyl group,9-benzo[g]chrysenyl group, 10-benzo[g]chrysenyl group,11-benzo[g]chrysenyl group, 12-benzo[g]chrysenyl group,13-benzo[g]chrysenyl group, 14-benzo[g]chrysenyl group, 1-triphenylenylgroup, 2-triphenylenyl group, 2-fluorenyl group, benzofluorenyl group,dibenzofluorenyl group, 2-biphenylyl group, 3-biphenylyl group,4-biphenylyl group, p-terphenyl-4-yl group, p-terphenyl-3-yl group,p-terphenyl-2-yl group, m-terphenyl-4-yl group, m-terphenyl-3-yl group,m-terphenyl-2-yl group or the like can be given.

The aryl group has preferably 6 to 20, further preferably 6 to 10 ringcarbon atoms. Preferable aryl groups area phenyl group and a naphthylgroup.

The arylsilyl group is represented by —SiZ₃, and examples of Z are thesame as those of the aryl group.

The alkoxy group is represented by —OY, and examples of Y are the sameas those of the alkyl or aryl group.

The aralkyl group is represented by —Y—Z, and examples of Y includealkylene groups corresponding to the examples of the alkyl group, andexamples of Z are the same as those of the aryl group.

Examples of the cycloalkyl group include a cyclopropyl group, cyclobutylgroup, cyclopentyl group, cyclohexyl group, 4-methylcyclohexyl group,1-adamantyl group, 2-adamantyl group, 1-norbornyl group and 2-norbornylgroup. The cycloalkyl group has preferably 3 to 10 ring carbon atoms,and further preferably 5 to 8 ring carbon atoms.

Specific examples of the aromatic amine derivatives are given below.

No specific restrictions are imposed on the aromatic amine derivative ofthe invention. For example, it can be produced from 1,6-dibromopyrene(Journal of Chemical Society, Perkin I, page 1622 (1072) or the like).

The aromatic amine derivative of the invention is suitable as thematerial for an organic electroluminescence device. In particular, it ispreferable to use it as a doping material for the emitting layer. Byusing it in the emitting layer, an organic electroluminescence devicewhich can emit blue light having a shorter wavelength as compared withconventional devices can be obtained.

It is preferred that the aromatic amine derivative of the invention becombined with an anthracene derivative represented by the followingformula (10) and be used as a material for an organicelectroluminescence device.

In the formula (10), Ar¹¹ and Ar¹² are independently a substituted orunsubstituted aryl group having 6 to 30 ring carbon atoms or asubstituted or unsubstituted heterocyclic group having 5 to 30 ringatoms, and

R¹⁰¹ to R¹⁰⁸ are independently a hydrogen atom, a fluorine atom, asubstituted or unsubstituted alkyl group having 1 to 10 carbon atoms, asubstituted or unsubstituted cycloalkyl group having 3 to 10 carbonatoms, a substituted or unsubstituted alkylsilyl group having 3 to 30carbon atoms, a substituted or unsubstituted arylsilyl group having 8 to30 ring carbon atoms, a substituted or unsubstituted alkoxy group having1 to 20 carbon atoms, a substituted or unsubstituted aryloxy grouphaving 6 to 20 ring carbon atoms, a substituted or unsubstituted arylgroup having 6 to 30 ring carbon atoms, or a substituted orunsubstituted heterocyclic group having 5 to 30 ring atoms.

In the formula (10), it is preferred that Ar¹¹ and Ar¹² be independentlya substituted or unsubstituted fused aromatic ring group having 10 to 30ring carbon atoms.

In the formula (10), it is preferred that Ar¹¹ be a substituted orunsubstituted phenyl group and Ar¹² be a substituted or unsubstitutedfused aromatic ring group having 10 to 30 ring carbon atoms.

In the anthracene derivative represented by the formula (10), Ar¹¹ andAr¹² are independently a group formed of 1 to 4 aromatic hydrocarbonrings which may independently be substituted. The group formed of 1 to 4aromatic hydrocarbon rings is, for example, benzene, naphthalene,phenanthrene, fluorene, anthracene, benzoanthracene or a combination of2 or 2 or more selected from them. The aromatic hydrocarbon ring ispreferably a benzene ring. For example, benzene, naphthalene, acombination of benzene and naphthalene or benzanthracene can bementioned. Specific examples thereof include a phenyl group, 1-naphthylgroup, 2-naphthyl group, 1-naphthylphenyl group, 2-naphthylphenyl groupand benzoanthracenyl group. As the substituent of these groups, an alkylgroup having 1 to 4 carbon atoms, a silyl group, a silyl groupsubstituted by an alkyl group having 1 to 4 carbon atoms, or the likecan be mentioned.

Further, it is preferred that R¹⁰¹ to R¹⁰⁸ be independently a hydrogenatom, an alkyl group having 1 to 4 carbon atoms, a silyl group or asilyl group which is substituted by an alkyl group having 1 to 4 carbonatoms. A hydrogen atom is particularly preferable.

It is preferred that the anthracene derivative represented by theformula (10) be one of the following anthracene derivatives (A), (B) and(C). An anthracene derivative is selected according to the configurationor the required properties of an organic EL device to which theanthracene derivative is used.

(Anthracene Derivative (A))

In this anthracene derivative, Ar¹¹ and Ar¹² in the formula (10) areindependently a substituted or unsubstituted fused aromatic ring grouphaving 10 to 30 ring carbon atoms. This anthracene derivative can bedivided into one in which Ar¹¹ and Ar¹² are the same substituted orunsubstituted fused aromatic ring group and one in which Ar¹¹ and Ar¹²are different substituted or unsubstituted fused aromatic ring groups.

Specific examples of the anthracene derivative (A) include anthracenederivatives represented by the following formulas (10-1) to (10-3).

The anthracene derivative represented by the following formula (10-1) isan anthracene derivative in which Ar¹¹ and Ar¹² in the formula (10) area substituted or unsubstituted 9-phenanthrenyl group.

In the formula (10-1), R¹⁰¹ to R¹⁰⁸ are the same as mentioned above.

R¹¹¹ is a substituted or unsubstituted aryl group having 6 to 30 ringcarbon atoms, a substituted or unsubstituted heterocyclic group having 5to 30 ring atoms, a substituted or unsubstituted alkyl group having 1 to10 carbon atoms, a substituted or unsubstituted cycloalkyl group having3 to 10 ring carbon atoms, a substituted or unsubstituted alkoxy grouphaving 1 to 20 carbon atoms, a substituted or unsubstituted silyl group,a cyano group or a fluorine atom.

a is an integer of 0 to 9, and when a is an integer of 2 or more, pluralR¹¹¹s may be the same or different on the condition that 2 substitutedor unsubstituted phenanthrenyl groups are the same.

The anthracene derivative represented by the following formula (10-2) isan anthracene derivative in which Ar¹¹ and Ar¹² in the formula (10) area substituted or unsubstituted 2-naphthyl group.

In the formula (10-2), R¹⁰¹ to R¹⁰⁸ and R¹¹¹ are as those mentionedabove, and b is an integer of 0 to 7. When b is an integer of 2 or more,plural R¹¹¹s may be the same or different on the condition that twosubstituted or unsubstituted 2-naphthyl groups are the same.

The anthracene derivative represented by the following formula (10-3) isan anthracene derivative in which Ar¹¹ and Ar¹² in the formula (10) area substituted or unsubstituted 1-naphthyl group.

In the formula (10-3), R¹⁰¹ to R¹⁰⁸, R¹¹¹ and b are as those mentionedabove. When b is an integer of 2 or more, plural R¹¹¹s may be the sameor different on the condition that two substituted or unsubstituted1-naphthyl groups are the same.

As for the anthracene derivative in which Ar¹¹ and Ar¹² in the formula(10) are different substituted or unsubstituted fused aromatic ringgroups, it is preferred that Ar¹¹ and Ar¹² be one of a substituted orunsubstituted 9-phenanthryl group, a substituted or unsubstituted1-naphthyl group or a substituted or unsubstituted 2-naphthyl group.

Specifically, this anthracene derivative is divided into one in whichAr¹¹ is a 1-naphthyl group and Ar¹² is a 2-naphthyl group, one in whichAr¹¹ is a 1-naphthyl group and Ar¹² is a 9-phenanthryl group, and one inwhich Ar¹¹ is a 2-naphthyl group and Ar¹² is a 9-phenanthryl group.

(Anthracene Derivative (B))

This anthracene derivative is an anthracene derivative in which one ofAr¹¹ and Ar¹² in the formula (10) is a substituted or unsubstitutedphenyl group, and the other is a substituted or unsubstituted fusedaromatic ring group having 10 to 50 ring carbon atoms. Specific examplesof the anthracene derivative include anthracene derivatives representedby the following formulas (10-4) and (10-5).

In the anthracene derivative represented by the following formula(10-4), Ar¹¹ in the formula (10) is a substituted or unsubstituted1-naphthyl group and Ar¹² in the formula (10) is a substituted orunsubstituted phenyl group.

In the formula (10-4), R¹⁰¹ to R¹⁰⁸ and R¹¹¹ are as those in theformulas (10) and (10-1).

b is an integer of 0 to 7, and when b is an integer of 2 or more, pluralR¹¹¹s may be the same or different.

Ar⁶ is a substituted or unsubstituted aryl group having 6 to 30 ringcarbon atoms, a substituted or unsubstituted alkyl group having 1 to 10carbon atoms, a substituted or unsubstituted cycloalkyl group having 3to 10 ring carbon atoms or a substituted or unsubstituted heterocyclicgroup having 5 to 30 ring atoms. Ar⁶ may form a bond with a benzene ringto which it bonds. For example, Ar⁶ may form a ring such as asubstituted or unsubstituted fluorenyl group or a substituted orunsubstituted dibenzofuranyl group. Preferable examples of Ar⁶ include a9,9-dimethylfluorene-1-yl group, a 9,9-dimethylfluorene-2-yl group, a9,9-dimethylfluorene-3-yl group, a 9,9-dimethylfluorene-4-yl group, adibenzofuran-1-yl group, a dibenzofuran-2-yl group, a dibenzofuran-3-ylgroup or a dibenzofuran-4-yl group.

The anthracene derivative represented by the following formula (10-5) isan anthracene derivative in which Ar¹¹ in the formula (10) is asubstituted or unsubstituted 2-naphthyl group and Ar¹² in the formula(10) is a substituted or unsubstituted phenyl group.

In the formula (10-5), R¹⁰¹ to R¹⁰⁸, R¹¹¹ and b are as those mentionedabove.

Ar⁷ is a substituted or unsubstituted aryl group having 6 to 30 ringcarbon atoms, a substituted or unsubstituted alkyl group having 1 to 10carbon atoms, a substituted or unsubstituted cycloalkyl group having 3to 10 ring carbon atoms or a substituted or unsubstituted heterocyclicgroup having 5 to 30 ring atoms. Ar⁷ may form a ring with a benzene ringto which it bonds.

Preferred examples of Ar⁷ include a dibenzofuran-1-yl group, adibenzofuran-2-yl group, a dibenzofuran-3-yl group and adibenzofuran-4-yl group.

Ar⁷ may form a ring such as a substituted or unsubstituted fluorenylgroup or a substituted or unsubstituted dibenzofuranyl group with abenzene ring to which it bonds. If b is an integer of 2 or more, pluralR¹¹¹s may be the same or different.

(Anthracene Derivative (C))

This anthracene derivative is represented by the following formula(10-6). Specifically, it is preferred that the anthracene derivative bea derivative represented by one of the following formulas (10-6-1),(10-6-2) and (10-6-3).

In the formula (10-6), R¹⁰¹ to R¹⁰⁸ are the same as those mentionedabove. Ar⁸ is the same as Ar⁶.

Ar⁹ is a substituted or unsubstituted aryl group having 6 to 30 ringcarbon atoms, a substituted or unsubstituted alkyl group having 1 to 10carbon atoms, a substituted or unsubstituted cycloalkyl group having 3to 10 ring carbon atoms or a substituted or unsubstituted heterocyclicgroup having 5 to 50 ring atoms.

Ar⁸ and Ar⁹ are independently selected.

In the formula (10-6-1), R¹⁰¹ to R¹⁰⁸ are the same as those definedabove.

In the formula (10-6-2), R¹⁰¹ to R¹⁰⁸ are the same as those definedabove. Ar¹⁰ is a substitute or unsubstituted fused aromatic ring grouphaving 10 to 20 ring carbon atoms.

In the formula (10-6-3), R¹⁰¹ to R¹⁰⁸ are the same as those in theformula (10).

Ar^(5a) and Ar^(6a) are independently a substituted or unsubstitutedfused aromatic ring group having 10 to 20 ring carbon atoms.

Further, the following anthracene derivatives (10-7) to (10-8) arepreferable.

In the formula (10-7), R¹⁰¹ to R¹⁰⁸ and Ar¹² are the same as those inthe formula (10).

L is a single bond, a substituted or unsubstituted arylene group having6 to 30 ring carbon atoms or a divalent substituted or unsubstitutedheterocyclic group having 5 to 30 ring atoms.

R¹²¹ is a substituted or unsubstituted aryl group having 6 to 30 ringcarbon atoms, a substituted or unsubstituted heterocyclic group having 5to 30 ring atoms, a substituted or unsubstituted alkyl group having 1 to10 carbon atoms, a substituted or unsubstituted cycloalkyl group having3 to 10 ring carbon atoms, a substituted or unsubstituted alkoxy grouphaving 1 to 20 carbon atoms, a substituted or unsubstituted silyl group,a cyano group or a fluorine atom.

n is an integer of 0 to 11. If n is an integer of 2 or more, pluralR¹²¹s may be the same or different. Preferably, n is 1 to 2.

In the formula (10-8), R¹⁰¹ to R¹⁰⁸ and Ar¹² are the same as those inthe formula (10). L and R¹²¹ are the same as those in the formula(10-7).

X¹¹ is an oxygen atom, a sulfur atom or —NR—. R is the same as R¹⁰¹ toR¹⁰⁸.

m is an integer of 0 to 7. If m is an integer of 2 or more, plural R¹²¹smay be the same or different. Preferably, m is 1 to 2.

Further, as in the anthracene derivative (10-9) shown below, it ispreferred that, in the anthracene derivative (10), Ar¹¹ be anunsubstituted phenyl group and Ar¹² be a substituted or unsubstitutedaryl group having 6 to 30 ring carbon atoms or a substituted orunsubstituted heterocyclic group having 5 to 30 ring atoms.

In the formula (10-9), R¹⁰¹ to R¹⁰⁸ and Ar¹² are the same as those inthe formula (10).

Similarly, as in the anthracene derivative (10-10) shown below, it ispreferred that, in the anthracene derivative (10), it is preferred thatAr¹¹ be an unsubstituted phenanthrenyl group, and Ar¹² be a substitutedor unsubstituted aryl group having 6 to 30 ring carbon atoms or asubstituted or unsubstituted heterocyclic group having 5 to 30 ringatoms.

In the formula (10-10), R¹⁰¹ to R¹⁰⁸ and Ar¹² are the same as those inthe formula (10).

As examples of the aryl group having 6 to 30 ring carbon atomsrepresented by R¹⁰¹ to R¹⁰⁸, R¹¹¹, R¹²¹, Ar⁵ to Ar⁹, Ar¹¹ and Ar¹², aphenyl group, a naphthyl group, an anthryl group, a phenanthryl group, anaphthacenyl group, a pyrenyl group, a chrysenyl group, abenzo[c]phenanthryl group, a benzo[g]chrysenyl group, a triphenylenylgroup, a fluorenyl group, a 9,9-dimethylfluorene-2-yl group, abenzofluorenyl group, a dibenzofluorenyl group, a benzo[a]anthryl group,a biphenylyl group, a p-terphenyl-4-yl group, a p-terphenyl-3-yl group,a p-terphenyl-2-yl group, a m-terphenyl-4-yl group, a m-terphenyl-3-ylgroup, a m-terphenyl-2-yl group, an o-tolyl group, an m-tolyl group, ap-tolyl group, a p-t-butylphenyl group, a p-(2-phenylpropyl)phenylgroup, a 3-methyl-2-naphthyl group, a 4-methyl-1-naphthyl group, a4-methyl-1-anthryl group, a 4′-methylbiphenylyl group, a4″-t-butyl-p-terphenyl-4-yl group or the like can be given. The fusedaromatic ring group having 10 to 30 ring carbon atoms means a group, ofthe above-mentioned aryl groups, in which two or more ring structuresare fused. Examples thereof include a naphthyl group, a phenanthrylgroup, an anthryl group, a chrysenyl group, a benzoanthryl group, abenzophenanthryl group, a triphenylenyl group, a benzochrysenyl group,an indenyl group, a fluorenyl group, a 9,9-dimethylfluorenyl group, abenzofluorenyl group, a dibenzofluorenyl group, a fluoranthenyl groupand a benzofluoranthenyl group.

The fused aromatic ring group is preferably an unsubstituted phenylgroup, a substituted phenyl group and a substituted or unsubstitutedaryl group having 10 to 14 ring carbon atoms (for example, a 1-naphthylgroup, a 2-naphthyl group and a 9-phenanthryl group), a substituted orunsubstituted fluorenyl group (2-fluorenyl group) and a substituted orunsubstituted pyrenyl group (1-pyrenyl group, 2-pyrenyl group and4-pyrenyl group).

The aryl group having 6 to 30 ring carbon atoms may be substituted by asubstituent such as an alkyl group, a cycloalkyl group, an aryl groupand a heterocyclic group. Examples of the substituents are the same asthe substituents mentioned above. As the substituent, an aryl group anda heterocyclic group are preferable.

As the fused aromatic ring group having 10 to 20 ring carbon atomsrepresented by Ar^(5a), Ar^(6a) and Ar¹⁰, a naphthyl group, an anthrylgroup, a phenanthryl group, a naphthacenyl group, a pyrenyl group, afluorenyl group or the like can be given. In particular, a 1-naphthylgroup, a 2-naphthyl group, a 9-phenanthryl group and a fluorenyl group(2-fluorenyl group) are preferable. The fused aromatic ring group having10 to 20 ring carbon atoms may be substituted by a substituent such asan alkyl group, a cycloalkyl group, an aryl group or a heterocyclicgroup. Examples of the substituents are the same as the substituentsmentioned above. As the substituent, an aryl group and a heterocyclicgroup are preferable.

Examples of the heterocyclic group having 5 to 30 ring atoms of R¹⁰¹ toR¹⁰⁸, R¹¹¹, Ar⁵ to Ar⁶ and Ar¹¹ to Ar¹² include a pyrrolyl group,pyrazinyl group, pyridinyl group, indolyl group, isoindolyl group, furylgroup, benzofuranyl group, isobenzofuranyl group, dibenzofuranyl group,dibenzothiophenyl group, quinolyl group, isoquinolyl group, quinoxalinylgroup, carbazolyl group, phenanthrydinyl group, acridinyl group,phenanthronyl group, phenazinyl group, phenothiazinyl group,phenoxazinyl group, oxazolyl group, oxadiazolyl group, furazanyl group,thienyl group, methylpyrrolyl group, 2-t-butylpyrrolyl group,3-(2-phenylpropyl)pyrrolyl group, 2-methyl-1-indolylgroup,4-methyl-1-indolyl group, 2-methyl-3-indolyl group, 4-methyl-3-indolylgroup, 2-t-butyl-1-indolyl group, 4-t-butyl-1-indolyl group,2-t-butyl-3-indolyl group and 4-t-butyl-3-indolyl group. Of these, a1-benzofuranyl group, 2-benzofuranyl group, 3-benzofuranyl group,4-benzofuranyl group, 1-dibenzothiophenyl group, 2-dibenzothiophenylgroup, 3-dibenzothiophenyl group, 4-dibenzothiophenyl group,1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group, 4-carbazolylgroup and 9-carbozolyl group are preferable.

The heterocyclic group having 5 to 30 ring atoms may be substituted by asubstituent such as an alkyl group, cycloalkyl group, aryl group andheterocyclic group, and examples of the substituent include the samegroups as the above-mentioned substituents. As the substituent, an arylgroup and a heterocyclic group are preferable.

Examples of the alkyl group having 1 to 10 carbon atoms of R¹⁰¹ to R¹⁰⁸,R¹¹¹, R¹²¹, and Ar⁵ to Ar⁹ include a methyl group, ethyl group, propylgroup, isopropyl group, n-butyl group, s-butyl group, isobutyl group,t-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octylgroup, hydroxymethyl group, 1-hydroxyethyl group, 2-hydroxyethyl group,2-hydroxyisobutyl group, 1,2-dihydroxyethyl group,1,3-dihydroxyisopropyl group, 2,3-dihydroxy-t-butyl group,1,2,3-trihydroxypropyl group, aminomethyl group, 1-aminoethyl group,2-aminoethyl group, 2-aminoisobutyl group, 1,2-diaminoethyl group,1,3-diaminoisopropyl group, 2,3-diamino-t-butyl group,1,2,3-triaminopropyl group, cyanomethyl group, 1-cyanoethyl group,2-cyanoethyl group, 2-cyanoisobutyl group, 1,2-dicyanoethyl group,1,3-dicyanoisopropyl group, 2,3-dicyano-t-butyl group and1,2,3-tricyanopropyl group.

Of these, a methyl group, ethyl group, propyl group, isopropyl group,n-butyl group, s-butyl group, isobutyl group and t-butyl group arepreferable. The alkyl group having 1 to 10 carbon atoms may besubstituted by a substituent such as an alkyl group, cycloalkyl group,aryl group and heterocyclic group, and examples of the substituentinclude the same groups as the above-mentioned substituents. As thesubstituent, an aryl group and a heterocyclic group are preferable.

Examples of the cycloalkyl group having 3 to 10 ring carbon atoms ofR¹⁰¹ to R¹⁰⁸, R¹¹¹, R¹²¹, and Ar⁵ to Ar⁹ include a cyclopropyl group,cyclobutyl group, cyclopentyl group, cyclohexyl group,4-methylcyclohexyl group, 1-adamantyl group, 2-adamantyl group,1-norbornyl group and 2-norbornyl group. Of these, cyclopentyl andcyclohexyl are preferable. The cycloalkyl group having 3 to 8 ringcarbon atoms may be substituted by a substituent such as an alkyl group,cycloalkyl group, aryl group and heterocyclic group, and examples of thesubstituent include the same groups as the above-mentioned substituents.As the substituent, an aryl group and heterocyclic group are preferable.

Examples of the alkylsilyl group and arylsilyl group of R¹⁰¹ to R¹⁰⁸,R¹¹¹, and R¹²¹ include a trimethylsilyl group, triethylsilyl group,t-butyldimethylsilyl group, vinyldimethylsilyl group,propyldimethylsilyl group and triphenylsilyl group. The silyl group maybe substituted by a substituent such as an alkyl group, cycloalkylgroup, aryl group and heterocyclic group, and examples of thesubstituent include the same groups as the above-mentioned substituents.As the substituent, an aryl group and a heterocyclic group arepreferable.

The alkoxy group having 1 to 20 carbon atoms of R¹⁰¹ to R¹⁰⁸, R¹¹¹ andR¹²¹ is represented by —OZ, and Z is selected from the substituted orunsubstituted alkyl group of R¹⁰¹ to R¹⁰⁸. The alkyl group may besubstituted by a substituent such as an alkyl group, cycloalkyl group,aryl group and heterocyclic group, and examples of the substituentinclude the same groups as the above-mentioned substituents. As thesubstituent, an aryl group and heterocyclic group are preferable.

The aryloxy group having 6 to 20 carbon atoms of R¹⁰¹ to R¹⁰⁸, R¹¹¹ andR¹²¹ is represented by —OZ, and Z is selected from the substituted orunsubstituted aryl group of R¹⁰¹ to R¹⁰⁸. The aryl group may besubstituted by a substituent such as an alkyl group, cycloalkyl group,aryl group and heterocyclic group, and examples of the substituentinclude the same groups as the above-mentioned substituents. As thesubstituent, an aryl group and a heterocyclic group are preferable.

As the substituted or unsubstituted arylene group having 6 to 30 ringcarbon atoms or the substituted or unsubstituted divalent heterocyclicgroup having 5 to 30 ring atoms of L in formulas (10-7) and (10-8),divalent groups of the aryl group and heterocyclic group described abovecan be given.

Specific examples of the anthracene derivative represented by theformula (10) can be given as follows:

When the aromatic amine derivative of the invention is contained as adoping material (dopant), the amount thereof is preferably 0.1 to 20mass %, more preferably 1 to 10 mass %.

To the material for an organic EL device (organic luminescent medium) ofthe invention, a known material for an organic EL may be added, ifnecessary. For example, a hole-transporting material having abisarylamino structure or a N-arylcarbazolyl structure, or anelectron-transporting compound having a benzimidazolyl structure may beadded.

Specifically, materials forming a hole-injecting/transporting layer,mentioned later, or an electron-injecting material may be used.

The organic EL device of the invention comprises one or more organicthin film layers comprising an emitting layer between an anode and acathode. At least one layer of the organic thin film layers contains thearomatic amine derivative of the invention singly or as a component of amixture.

The aromatic amine derivative of the invention and the anthracenederivative mentioned above may be used in a hole-injecting layer, ahole-transporting layer, an electron-injecting layer, and anelectron-transporting layer in addition to an emitting layer.

In the invention, as the organic EL device in which the organic thinfilm layer is composed of plural layers, one in which layers aresequentially stacked (anode/hole-injecting layer/emittinglayer/cathode), (anode/emitting layer/electron-injecting layer/cathode),(anode/hole-injecting layer/emitting layer/electron-injectinglayer/cathode), (anode/hole-injecting layer/hole-transportinglayer/emitting layer/electron-injecting layer/cathode) or the like canbe given.

By allowing the organic thin film layer to be composed of plural layers,the organic EL device can be prevented from lowering of luminance orlifetime due to quenching. If necessary, an emitting material, a dopingmaterial, a hole-injecting material or an electron-injecting materialcan be used in combination. Further, due to the use of a dopingmaterial, luminance or luminous efficiency may be improved. Thehole-injecting layer, the emitting layer and the electron-injectinglayer may respectively be formed of two or more layers. In such case, inthe hole-injecting layer, a layer which injects holes from an electrodeis referred to as a hole-injecting layer, and a layer which receivesholes from the hole-injecting layer and transports the holes to theemitting layer is referred to as a hole-transporting layer. Similarly,in the electron-injecting layer, a layer which injects electrons from anelectrode is referred to as an electron-injecting layer and a layerwhich receives electrons from an electron-injecting layer and transportsthe electrons to the emitting layer is referred to as anelectron-transporting layer. Each of these layers is selected and usedaccording to each of the factors of a material, i.e. the energy level,heat resistance, adhesiveness to the organic layer or the metalelectrode or the like.

Examples of the material other than the above anthracene derivativewhich can be used in the emitting layer together with the aromatic aminederivative of the invention include, though not limited thereto, fusedpolycyclic aromatic compounds such as naphthalene, phenanthrene,rubrene, tetracene, pyrene, perylene, chrysene, decacyclene, coronene,tetraphenylcyclopentadiene, pentaphenylcyclopentadiene, fluorene,spirofluorene and derivatives thereof, organic metal complexes such astris(8-quinolinolate)aluminum, triarylamine derivatives, styrylaminederivatives, stilbene derivatives, coumarin derivatives, pyranederivatives, oxazone derivatives, benzothiazole derivatives, benzoxazolederivatives, benzimidazole derivatives, pyrazine derivatives, cinnamatederivatives, diketo-pyrrolo-pyrrole derivatives, acrylidone derivativesand quinacrylidone derivatives.

As the hole-injecting material, a compound which can transport holes,exhibits hole-injecting effects from the anode and excellenthole-injection effect for the emitting layer or the emitting material,and has an excellent capability of forming a thin film is preferable.Specific examples thereof include, though not limited thereto,phthalocyanine derivatives, naphthalocyanine derivatives, porphylinederivatives, benzidine-type triphenylamine, diamine-type triphenylamine,hexacyanohexaazatriphenylene, derivatives thereof, and polymer materialssuch as polyvinylcarbazole, polysilane and conductive polymers.

Of the hole-injecting materials usable in the organic EL device of theinvention, further effective hole-injecting materials are phthalocyaninederivatives.

Examples of the phthalocyanine (Pc) derivative include, though notlimited thereto, phthalocyanine derivatives such as H₂Pc, CuPc, CoPc,NiPc, ZnPc, PdPc, FePc, MnPc, ClAlPc, ClGaPc, ClInPc, ClSnPc, Cl₂SiPc,(HO)AlPc, (HO)GaPc, VOPc, TiOPc, MoOPc and GaPc-O-GaPc, andnaphthalocyanine derivatives.

In addition, it is also possible to sensitize carriers by adding to thehole-injecting material an electron-accepting substance such as a TCNQderivative.

Preferable hole-transporting materials usable in the organic EL deviceof the invention are aromatic tertiary amine derivatives.

Examples of the aromatic tertiary amine derivative include, though notlimited thereto,N,N′-diphenyl-N,N′-dinaphthyl-1,1′-biphenyl-4,4′-diamine,N,N,N′,N′-tetrabiphenyl-1,1′-biphenyl-4,4′-diamine or an oligomer or apolymer having these aromatic tertiary amine skeletons.

As the electron-injecting material, a compound which can transportelectrons, exhibits electron-injecting effects from the cathode andexcellent electron-injection effect for the emitting layer or theemitting material, and has an excellent capability of forming a thinfilm is preferable.

In the organic EL device of the invention, further effectiveelectron-injecting materials are a metal complex compound and anitrogen-containing heterocyclic derivative.

Examples of the metal complex compound include, though not limitedthereto, 8-hydroxyquinolinate lithium, bis(8-hydroxyquinolinate)zinc,tris(8-hydroxyquinolinate)aluminum, tris(8-hydroxyquinolinate)gallium,bis(10-hydroxybenzo[h]quinolinate)beryllium andbis(10-hydroxybenzo[h]quinolinate)zinc.

As examples of the nitrogen-containing heterocyclic derivative, oxazole,thiazole, oxadiazole, thiadiazole, triazole, pyridine, pyrimidine,triazine, phenanthroline, benzimidazole, imidazopyridine or the like arepreferable, for example. Of these, a benzimidazole derivative, aphenanthroline derivative and an imidazopyridine derivative arepreferable.

As a preferred embodiment, a dopant is further contained in theseelectron-injecting materials, and in order to facilitate receivingelectrons from the cathode, it is further preferable to dope thevicinity of the cathode interface of the second organic layer with adopant, the representative example of which is an alkali metal.

As the dopant, a donating metal, a donating metal compound and adonating metal complex can be given. These reducing dopants may be usedsingly or in combination of two or more.

In the organic EL device of the invention, the emitting layer maycontain, in addition to at least one of the above-mentioned aromaticamine derivatives represented by the formulas (1) to (4), at least oneof an emitting material, doping material, hole-injecting material,hole-transporting material and electron-injecting material in the samelayer. Moreover, for improving stability of the organic EL deviceobtained by the invention to temperature, humidity, atmosphere, etc. itis also possible to prepare a protective layer on the surface of thedevice, and it is also possible to protect the entire device by applyingsilicone oil, resin, etc.

As the conductive material used in the anode of the organic EL device ofthe invention, a conductive material having a work function of more than4 eV is suitable. Carbon, aluminum, vanadium, iron, cobalt, nickel,tungsten, silver, gold, platinum, palladium or the like, alloys thereof,oxidized metals which are used in an ITO substrate and a NESA substratesuch as tin oxide and indium oxide and organic conductive resins such aspolythiophene and polypyrrole are used. As the conductive material usedin the cathode, a conductive material having a work function of smallerthan 4 eV is suitable. Magnesium, calcium, tin, lead, titanium, yttrium,lithium, ruthenium, manganese, aluminum, and lithium fluoride or thelike, and alloys thereof are used, but not limited thereto.Representative examples of the alloys include, though not limitedthereto, magnesium/silver alloys, magnesium/indium alloys andlithium/aluminum alloys. The amount ratio of the alloy is controlled bythe temperature of the deposition source, atmosphere, vacuum degree orthe like, and an appropriate ratio is selected. If necessary, the anodeand the cathode each may be composed of two or more layers.

In the organic EL device of the invention, in order to allow it to emitlight efficiently, it is preferred that at least one of the surfaces befully transparent in the emission wavelength region of the device. Inaddition, it is preferred that the substrate also be transparent. Thetransparent electrode is set such that predetermined transparency can beensured by a method such as deposition or sputtering by using theabove-mentioned conductive materials. It is preferred that the electrodeon the emitting surface have a light transmittance of 10% or more.Although no specific restrictions are imposed on the substrate as longas it has mechanical and thermal strength and transparency, a glasssubstrate and a transparent resin film can be given.

Each layer of the organic EL device of the invention can be formed by adry film-forming method such as vacuum vapor deposition, sputtering,plasma, ion plating or the like or a wet film-forming method such asspin coating, dipping, flow coating or the like. Although the filmthickness is not particularly limited, it is required to adjust the filmthickness to an appropriate value. If the film thickness is too large, alarge voltage is required to be applied in order to obtain a certainoptical output, which results in a poor efficiency. If the filmthickness is too small, pinholes or the like are generated, and asufficient luminance cannot be obtained even if an electrical field isapplied. The suitable film thickness is normally 5 nm to 10 μm, with arange of 10 nm to 0.2 μm being further preferable.

In the case of the wet film-forming method, a thin film formed bydissolving or dispersing materials forming each layer in an appropriatesolvent such as ethanol, chloroform, tetrahydrofuran and dioxane. Any ofthe above-mentioned solvents can be used.

As the solvent suited to such a wet film-forming method, a solutioncontaining the aromatic amine derivative of the invention as an organicEL material and a solvent can be used.

It is preferred that the organic EL material contain a host material anda dopant material, that the dopant material be the aromatic aminederivative of the invention, and that the host material be at least oneselected from the anthracene derivatives represented by the formula(10).

In each organic thin film layer, an appropriate resin or additive may beused in order to improve film-forming properties, to prevent generationof pinholes in the film, or for other purposes.

The organic EL device of the invention can be suitably used as a planaremitting body such as a flat panel display of a wall-hanging television,backlight of a copier, a printer or a liquid crystal display, lightsources for instruments, a display panel, a navigation light, or thelike. The compound of the invention can be used not only in an organicEL device but also in the field of an electrophotographic photoreceptor,a photoelectric converting element, a solar cell and an image sensor.

EXAMPLES Synthesis of Aromatic Amine Derivative Example 1

An aromatic amine derivative DM-1 was produced as below.

(1) Synthesis of 4-cyanophenylphenylamine

Under a flow of argon, in a 300 mL-recovery flask, 20 g of4-bromobenzonitrile, 30 mL of aniline, 1.50 g oftris(dibenzylideneacetone)dipalladium(0)[Pd₂(dba)₃], 2.1 g of2,2′-bis(diphenylphosphino)-1,1′-binaphthyl[BINAP], 21.1 g of sodiumtert-butoxide and 313 mL of dehydrated toluene were placed, and reactedat 85° C. for 6 hours.

After cooling, the reaction solution was filtered through celite. Thecrude product obtained was purified by means of silica-gelchromatography, and resulting solids were dried under reduced pressure,whereby 14.9 g of white solids were obtained (yield 70%).

(2) Synthesis of DM-1

Under a flow of argon, in a 300 mL-recovery flask, 7.2 g of4-cyanophenylphenylamine, 5.7 g of 1,6-dibromo-3,8-dimethylpyrene, 2.8 gof sodium tert-butoxide, 160 mg of palladium(II)acetate [Pd(OAc)₂], 135mg of tri-tert-butylphosphine and 73 mL of dehydrated toluene wereplaced, and reacted at 85° C. for 7 hours.

The reaction solution was filtered, and the crude product obtained waspurified by means of silica-gel chromatography. Solids obtained werere-crystallized with toluene, and resulting solids were dried underreduced pressure, whereby 2.6 g of yellow white solids were obtained. Asa result of FD-MS (Field desorption mass spectrometry), the resultingcompound was confirmed to be an intended product, which had an m/e of614 for the molecular weight 614.25.

Example 2

As shown below, an aromatic amine derivative DM-2 was produced in thesame manner as in Example 1, except that1,6-dibromo-3,8-diisopropylpyrene was used instead of1,6-dibromo-3,8-dimethylpyrene. As a result of mass spectroscopyanalysis, the resulting compound was confirmed to be an intendedproduct, which had an m/e of 670 for the molecular weight 670.31.

Example 3

An aromatic amine derivative DM-3 was produced as below.

(1) Synthesis of N-(4-(trimethylsilyl)phenyl)acetamide

Under a flow of argon, in a 1 L-recovery flask, 35 g of1-bromo-4-(trimethylsilyl)benzene, 22.6 g of acetamide, 5.8 g ofcopper(I)iodide, 42.2 g of potassium carbonate, and 380 mL of xylenewere placed. After stirring, 6.6 mL of N,N′-dimethylethylenediamine wasadded. The resultant was heated and stirred at reflux for 18 hours.

The reaction solution was filtered. The crude product obtained waswashed with toluene, clean water and methanol. Resulting solids weredried under reduced pressure, whereby 27 g of solids were obtained.

(2) Synthesis of N-(4-cyanophenyl)-N-(4-(trimethylsilyl)phenyl)acetamide

Under a flow of argon, in a 1 L-recovery flask, 27 g ofN-(4-(trimethylsilyl)phenyl)acetamide, 30 g of 4-bromobenzonitrile, 6.3g of copper (I) iodide, 45.6 g of potassium carbonate, and 412 mL ofxylene were placed. After stirring, 7.1 mL ofN,N′-dimethylethylenediamine was added. The resultant was heated andstirred at reflux for 18 hours.

The reaction solution was extracted with toluene and then filtered.After a filtrate was concentrated, a residue was purified by means ofsilica-gel chromatography to obtain 34 g of solids.

(3) Synthesis of (4-cyanophenyl)(4-trimethylsilylphenyl)amine

In a 300 mL-recovery flask, 34 g ofN-(4-cyanophenyl)-N-(4-(trimethylsilyl)phenyl)acetamide, 43 g ofpotassium hydroxide, 39 mL of clean water, 60 mL of toluene and 120 mLof ethanol were placed, and heated and stirred at reflux for 8 hours.

Ethyl acetate was added to the resultant, and separation and extractionwere conducted. After that, an organic phase was washed with clean waterand saturated saline, and dried with sodium sulfate. The crude productobtained by concentration was purified by means of silica-gelchromatography. Resulting solids were dried under reduced pressure,whereby 17 g of white solids were obtained (yield 59%).

(4) Synthesis of DM-3

Under a flow of argon, in a 300 mL-recovery flask, 7.5 g of(4-cyanophenyl)(4-trimethylsilylphenyl)amine, 5.0 g of1,6-dibromo-3,8-diisopropylpyrene, 2.2 g of sodium tert-butoxide, 130 mgof palladium(II)acetate[Pd(OAc)₂], 135 mg of tri-tert-butylphosphine and113 mL of dehydrated toluene were placed, and reacted at 85° C. for 7hours.

The reaction solution was filtered, and the crude product obtained waspurified by means of silica-gel chromatography. Solids obtained werere-crystallized with toluene, and resulting solids were dried underreduced pressure, whereby 8.0 g of yellow white solids were obtained. Asa result of FD-MS (Field desorption mass spectrometry), the resultingcompound was confirmed to be an intended product, which had an m/e of814 for the molecular weight 814.39.

Example 4

As shown below, an aromatic amine derivative DM-4 was produced in thesame manner as in Example 3, except that 4-bromobenzonitrile was usedinstead of 1-bromo-4-(trimethylsilyl)benzene, andN,N-bis(4-cyanophenyl)acetamide was synthesized. As a result of massspectroscopy analysis, the resulting compound was confirmed to be anintended product, which had an m/e of 720 for the molecular weight720.30.

Example 5

As below, an aromatic amine derivative DM-5 was produced in the samemanner as in Example 1, except that 2-bromofluorobenzene was usedinstead of 4-bromobenzonitrile, and (2-fluorophenyl)phenylamine wassynthesized. As a result of a mass spectroscopy analysis, the resultingcompound was confirmed to be an intended product, which had an m/e of656 for the molecular weight 656.30.

Fabrication of Organic EL Device Example 6

A glass substrate of 25 mm by 75 mm by 1.1 mm thick with an ITOtransparent electrode (anode) (GEOMATEC CO., LTD.) was subjected toultrasonic cleaning in isopropyl alcohol for 5 minutes, and cleaningwith UV/ozone for 30 minutes. The cleaned glass substrate withtransparent electrode lines was mounted on a substrate holder in avacuum deposition apparatus. First, compound A-1 was deposited on thesurface on which the transparent electrode lines were formed so as tocover the transparent electrode to form a 50 nm-thick film Subsequently,compound A-2 was deposited on the A-1 film to form a 45 nm-thick film.

Compound EM2 and compound DM-1 of the invention were deposited on theA-2 film into a thickness of 20 nm such that the film thickness ratio ofEM2 and DM-1 became 20:1 to form a blue emitting layer.

On this film, the following ET-1 was deposited into a thickness of 30 nmas an electron-transporting layer. Then, LiF was deposited into athickness of 1 nm. Metallic Al was deposited on the LiF film into athickness of 150 nm to form a metallic cathode, whereby an organic ELdevice was fabricated.

Examples 7 to 78, Comparative Examples 1 to 3

Organic EL devices were produced in the same manner as in Example 6,except that the host materials and doping materials shown in Tables 1and 2 were used.

The doping materials used in Comparative Examples 1 to 3 are shownbelow.

Current having a current density of 10 mA/cm² was applied to the organicEL devices produced in the Examples and Comparative Examples givenabove. Emission spectra thereof were measured with a spectroradiometer(CS1000, produced by MINOLTA), and external quantum efficiency wascalculated by the following formula (1).

The lifetime of the organic EL device was evaluated by measuring thehalf life at 500 cd/m² of initial luminance. The results are shown inTables 1 and 2.

$\begin{matrix}{{E.Q.E.} = {\frac{N_{P}}{N_{E}} \times 100}} \\{= {\frac{\frac{\left( {\pi/10^{9}} \right){\int{{\phi(\lambda)} \cdot {\mathbb{d}\lambda}}}}{hc}}{\frac{J/10}{e}} \times 100}} \\{= {\frac{\frac{\left( {\pi/10^{9}} \right){\sum\left( {{\phi(\lambda)} \cdot (\lambda)} \right)}}{hc}}{\frac{J/10}{e}} \times 100(\%)}}\end{matrix}$

-   N_(P): Number of photons-   N_(E): Number of electrons-   π: Circular constant=3.1416-   λ: Wavelength (nm)-   φ: Luminescence intensity (W/sr·m²·nm)-   h: Planck constant=6.63×10⁻³⁴ (J·s)-   c: Light velocity=3×10⁸ (m/s)-   J: Current density (mA/cm²)-   e: Charge=1.6×10⁻¹⁹ (C)

TABLE 1 Host Dopant CIEx CIEy EQE (%) Life (h) Example 6 EM2 DM-1 0.1370.098 7.2 3300 Example 7 EM9 DM-1 0.137 0.093 7.1 3300 Example 8 EM13DM-1 0.137 0.094 7.7 3900 Example 9 EM28 DM-1 0.137 0.094 7.7 4000Example 10 EM29 DM-1 0.137 0.093 7.2 3400 Example 11 EM31 DM-1 0.1370.094 7.7 4200 Example 12 EM32 DM-1 0.137 0.096 7.6 4100 Example 13 EM69DM-1 0.137 0.096 7.5 3800 Example 14 EM70 DM-1 0.137 0.094 7.5 3700Example 15 EM73 DM-1 0.137 0.096 7.6 3900 Example 16 EM78 DM-1 0.1370.096 7.5 3400 Example 17 EM82 DM-1 0.137 0.096 7.4 3400 Example 18EM125 DM-1 0.137 0.096 7.6 3800 Example 19 EM205 DM-1 0.137 0.096 7.43300 Example 20 EM360 DM-1 0.137 0.096 7.4 3100 Example 21 EM364 DM-10.137 0.101 7.1 2900 Example 22 EM367 DM-1 0.137 0.096 7.4 3100 Example23 EM372 DM-1 0.137 0.096 7.5 3100 Example 24 EM2 DM-2 0.137 0.098 7.23400 Example 25 EM9 DM-2 0.137 0.093 7.1 3400 Example 26 EM13 DM-2 0.1370.094 7.7 4000 Example 27 EM28 DM-2 0.137 0.094 7.7 4100 Example 28 EM29DM-2 0.137 0.093 7.2 3500 Example 29 EM31 DM-2 0.137 0.094 7.7 4300Example 30 EM32 DM-2 0.137 0.096 7.6 4200 Example 31 EM69 DM-2 0.1370.096 7.5 3900 Example 32 EM70 DM-2 0.137 0.094 7.5 3800 Example 33 EM73DM-2 0.137 0.096 7.6 4000 Example 34 EM78 DM-2 0.137 0.096 7.5 3500Example 35 EM82 DM-2 0.137 0.096 7.4 3500 Example 36 EM125 DM-2 0.1370.096 7.6 3900 Example 37 EM205 DM-2 0.137 0.096 7.4 3400 Example 38EM360 DM-2 0.137 0.096 7.4 3200 Example 39 EM364 DM-2 0.137 0.101 7.13000 Example 40 EM367 DM-2 0.137 0.096 7.4 3200 Example 41 EM372 DM-20.137 0.096 7.5 3200

TABLE 2 Host Dopant CIEx CIEy EQE (%) Life (h) Example 42 EM2 DM-3 0.1370.099 7.3 3300 Example 43 EM9 DM-3 0.137 0.094 7.2 3300 Example 44 EM13DM-3 0.137 0.095 7.8 3900 Example 45 EM28 DM-3 0.137 0.095 7.8 4000Example 46 EM29 DM-3 0.137 0.094 7.3 3400 Example 47 EM31 DM-3 0.1370.095 7.8 4200 Example 48 EM32 DM-3 0.137 0.097 7.7 4100 Example 49 EM69DM-3 0.137 0.097 7.6 3800 Example 50 EM70 DM-3 0.137 0.095 7.6 3700Example 51 EM73 DM-3 0.137 0.097 7.7 3900 Example 52 EM78 DM-3 0.1370.097 7.6 3400 Example 53 EM82 DM-3 0.137 0.097 7.5 3400 Example 54EM125 DM-3 0.137 0.097 7.7 3800 Example 55 EM205 DM-3 0.137 0.097 7.53300 Example 56 EM360 DM-3 0.137 0.097 7.5 3100 Example 57 EM364 DM-30.137 0.102 7.2 2900 Example 58 EM367 DM-3 0.137 0.097 7.5 3100 Example59 EM372 DM-3 0.137 0.097 7.6 3100 Example 60 EM2 DM-4 0.147 0.074 7.02300 Example 61 EM9 DM-4 0.147 0.069 6.9 2300 Example 62 EM13 DM-4 0.1470.070 7.5 2900 Example 63 EM28 DM-4 0.147 0.070 7.5 3000 Example 64 EM29DM-4 0.147 0.069 7.0 2400 Example 65 EM31 DM-4 0.147 0.070 7.5 3200Example 66 EM32 DM-4 0.147 0.072 7.4 3100 Example 67 EM69 DM-4 0.1470.072 7.3 2800 Example 68 EM70 DM-4 0.147 0.070 7.3 2700 Example 69 EM73DM-4 0.147 0.072 7.4 2900 Example 70 EM78 DM-4 0.147 0.072 7.3 2400Example 71 EM82 DM-4 0.147 0.072 7.2 2400 Example 72 EM125 DM-4 0.1470.072 7.4 2800 Example 73 EM205 DM-4 0.147 0.072 7.2 2300 Example 74EM360 DM-4 0.147 0.072 7.2 2100 Example 75 EM364 DM-4 0.147 0.077 6.91900 Example 76 EM367 DM-4 0.147 0.072 7.2 2100 Example 77 EM372 DM-40.147 0.072 7.3 2100 Example 78 EM28 DM-5 0.144 0.080 7.4 2100 Com. Ex.1 EM2 DM-C1 0.137 0.096 6.8 1000 Com. Ex. 2 EM2 DM-C2 0.126 0.175 6.51800 Com. Ex. 3 EM28 DM-C3 0.133 0.150 6.9 2500

As seen from Tables 1 and 2, by using the diaminopyrene derivative ofthe invention, an organic EL device capable emitting pure blue colorlight and having a long lifetime can be realized. As compared withComparative Example 1, it is clear that the diaminopyrene derivative ofthe invention which has a substituent at a mother nucleus enables anorganic EL device to have a significantly longer lifetime than thecompound having no substituent at a mother nucleus.

Furthermore, as compared with Comparative Example 2, the diaminopyrenederivative of the invention enables an organic EL device to emitsignificantly pure blue light and to have a longer lifetime than thecompound having no cyano group.

Comparison between Comparative Example 3 and Example 78 reveals that theorganic EL device using the compound in which at least one of Ar₁ to Ar₄is o-fluorophenyl can emit significantly pure blue light and has alonger lifetime than that using the compound in which at least one ofAr₁ to Ar₄ is p-fluorophenyl. Here, when lifetime is measured at thesame luminance, luminosity factor is likely to vary with an increase incolor purity. Therefore, a high current is required to be applied. Whena high current is applied, due to load imposed on the compound, thelifetime of the EL device tends to be short. As mentioned above, it hasbeen considered that it is difficult to achieve both high color purityand long lifetime. However, this can be achieved by using thediaminopyrene derivative of the invention.

Moreover, further significant effects are exhibited due to thecombination of a specific anthracene host. Of these, an anthracenederivative substituted by a fused ring, the representative examples ofwhich include EM28, EM29, EM31, EM32, EM69, EM70 and EM73, significantlycontributes to a prolongation of lifetime. Further preferable are1-naphthyl-substituted anthracene derivatives, the representativeexamples of which include EM28, EM29, EM31 and EM32. It is morepreferable to use the host material stated in the examples. However, theanthracene derivative which is within the scope of the claims of theinvention can be preferable used, since it can exhibit similaradvantageous effects.

As stated above, a display device which has a long lifetime and has highcolor reproducibility can be realized by the invention.

INDUSTRIAL APPLICABILITY

The organic EL device of the invention can be suitably used as a planaremitting body such as a flat panel display of a wall television,backlight of a copier, a printer, or a liquid crystal display, lightsources for instruments, a display panel, a navigation light, and thelike.

Although only some exemplary embodiments and/or examples of thisinvention have been described in detail above, those skilled in the artwill readily appreciate that many modifications are possible in theexemplary embodiments and/or examples without materially departing fromthe novel teachings and advantages of this invention. Accordingly, allsuch modifications are intended to be included within the scope of thisinvention.

The documents described in the specification are incorporated herein byreference in its entirety.

The invention claimed is:
 1. An aromatic amine derivative represented bythe following formula (1):

wherein R₁, R₃ to R₅, R₇ and R₈ are a hydrogen atom, R₂ and R₆ areindependently a hydrogen atom, a methyl group, an ethyl group, a propylgroup, an isopropyl group, a n-butyl group, a s-butyl group, an isobutylgroup, a t-butyl group, a n-pentyl group or a n-hexyl group, at leastone of R₂ and R₆ is a group other than a hydrogen atom, and Ar₁ to Ar₄are independently an unsubstituted phenyl group, or a phenyl groupsubstituted with one or more substituents selected from the groupconsisting of an alkyl group, an alkylsilyl group, a cyano group, ahalogen atom, a halogenated alkyl group, a nitro group and a carbonylgroup, at least one of A₁ to Ar₄ is a phenyl group substituted with oneor more substituents selected from the group consisting of a cyanogroup, a fluorine atom, a halogenated alkyl group, a nitro group and acarbonyl group, provided that, when at least one of Ar₁ to Ar₄ is ap-fluorophenyl group, at least one of Ar₁ to Ar₄ which are not ap-fluorophenyl group is a phenyl group other than a p-fluorophenyl groupwhich is substituted with one or more substituents selected from thegroup consisting of a cyano group, a fluorine atom, a halogenated alkylgroup, a nitro group and a carbonyl group.
 2. The aromatic aminederivative according to claim 1, which is represented by the followingformula (2):

wherein R₁ to R₈, are the same as those in the formula (1), Ar₂ and Ar₄are independently an unsubstituted phenyl group, or a phenyl groupsubstituted with one or more substituents selected from the groupconsisting of an alkyl group, an alkylsilyl group, a cyano group, ahalogen atom, a halogenated alkyl group and a nitro group, R₁₁ to R₂₀are independently a hydrogen atom, an alkyl group, an alkylsilyl group,a cyano group, a halogen atom, a halogenated alkyl group a nitro groupor a carbonyl group, and at least one of R₁₁ to R₂₀ is a cyano group, afluorine atom, a halogenated alkyl group, a nitro group or a carbonylgroup.
 3. The aromatic amine derivative according to claim 2, whereinAr₂ and Ar₄ are independently an unsubstituted phenyl group, or a phenylgroup substituted with one or more substituents selected from the groupconsisting of an alkyl group, an alkylsilyl group, a cyano group and afluorine atom.
 4. An organic electroluminescence device comprising acathode, an anode, and one or more organic thin film layers comprisingan emitting layer therebetween, wherein at least one layer of theorganic thin film layers comprises an aromatic amine derivativerepresented by the following formula (1) singly or as a component of amixture:

wherein R₁, R₃ to R₅, R₇ and R₈ are a hydrogen atom R₂ and R₆ areindependently a hydrogen atom, a methyl group, an ethyl group, a propylgroup, an isopropyl group, a n-butyl group, a s-butyl group, an isobutylgroup, a t-butyl group, a n-pentyl group or a n-hexyl group, at leastone of R₂ and R₆ is a group other than a hydrogen atom, and Ar₁ to Ar₄are independently an unsubstituted phenyl group, or a phenyl groupsubstituted with one or more substituents selected from the groupconsisting of an alkyl group, an alkylsilyl group, a cyano group, ahalogen atom, a halogenated alkyl group, a nitro group and a carbonylgroup, at least one of Ar₁ to Ar₄ is a phenyl group substituted with oneor more substituents selected from the group consisting of a cyanogroup, a fluorine atom, a halogenated alkyl group, a nitro group and acarbonyl group, provided that, when at least one of Ar₁ to Ar₄ is ap-fluorophenyl group, at least one of Ar₁ to Ar₄ which are not ap-fluorophenyl group is a phenyl group other than a p-fluorophenyl groupwhich is substituted with one or more substituents selected from thegroup consisting of a cyano group, a fluorine atom, a halogenated alkylgroup, a nitro group and a carbonyl group.
 5. The organicelectroluminescence device according to claim 4, wherein the emittinglayer comprises the aromatic amine derivative represented by the formula(1).
 6. The aromatic amine derivative according to claim 2, wherein A₂and A₄ are independently an unsubstituted phenyl group, or a phenylgroup substituted with one or more substituents selected from the groupconsisting of a methyl group, an ethyl group, a propyl group, anisopropyl group, a n-butyl group, a s-butyl group, an isobutyl group, at-butyl group, a n-pentyl group, a n-hexyl group, alkylsilyl group, acyano group and a flourine atom, R₁₁ to R₂₀ are independently a hydrogenatom, a methyl group, an ethyl group, a propyl group, an isopropylgroup, a n-butyl group, a s-butyl group, an isobutyl group, a t-butylnitro group or a carbonyl group, and at least one of R₁₁ to R₂₀ is acyano group, a fluorine atom, a nitro group or a carbonyl group.
 7. Thearomatic amine derivative according to claim 2, wherein A₂ and Ar₄ areindependently an unsubstituted phenyl group, or a phenyl groupsubstituted with one or more substituents selected from the groupconsisting of an alkyl group, an alkylsilyl group, a cyano group, ahalogen atom, a halogenated alkyl group and a nitro group, R₁₁ to R₂₀are independently a hydrogen atom or a cyano group, and at least one ofR₁₁ to R₁₅ is a cyano group, and at least one of R₁₆ to R₂₀ is a cyanogroup.
 8. The aromatic amine derivative according to claim 2, whereinAr₂ and Ar₄ are independently an unsubstituted phenyl group, or a phenylgroup substituted with one or more substituents selected from the groupconsisting of an alkyl group, an alkylsilyl group, a cyano group and afluorine atom, R₁₁ to R₂₀ are independently a hydrogen atom or a cyanogroup, and at least one of R₁₁ to R₁₅ is cyano group, and at least oneof R₁₆ to R₂₀ is a cyano group.
 9. The aromatic amine derivativeaccording to claim 2, wherein A₂ and Ar₄ are independently anunsubstituted phenyl group, or a phenyl group substituted with one ormore substituents selected from the group consisting of an alkyl group,an alkylsilyl group a cyano group, a halogen atom a halogenated alkylgroup and a nitro group, R₁₁, R₁₅, R₁₆ and R₂₀ are independently ahydrogen atom or a fluorine atom, R₁₂ to R₁₄ and R₁₇ to R₁₉ are ahydrogen atom, and at least one of R₁₁ and R₁₅ is a fluorine atom, andat least one of R₁₆ and R₂₀ is a fluorine atom.
 10. The aromatic aminederivative according to claim 2, wherein A₂ and Ar₄ are independently anunsubstituted phenyl group, or a phenyl group substituted with one ormore substituents selected from the group consisting of an alkyl group,an alkylsilyl group, a cyano group and a fluorine atom, R₁₁, R₁₅, R₁₆and R₂₀ are independently a hydrogen atom or a fluorine atom, R₁₂ to R₁₄and R₁₇ to R₁₉ are a hydrogen atom, and at least one of R₁₁ and R₁₅ is afluorine atom, and at least one of R₁₆ and R₂₀ is a fluorine atom. 11.The aromatic amine derivative according to claim 1, wherein the alkylgroup is a methyl group, an ethyl group, a propyl group, an isopropylgroup, a n-butyl group, a s-butyl group, an isobutyl group, a t-butylgroup, a n-pentyl group or a n-hexyl group, and the alkylsilyl group isrepresented by —SiY₃, and Y is independently methyl group, an ethylgroup, a propyl group, an isopropyl group, a n-butyl group, a s-butylgroup, an isobutyl group, a t-butyl group, a n-pentyl group or a n-hexylgroup.
 12. The organic electroluminescence device according to claim 4,wherein the aromatic amine derivative represented by the formula (1) isrepresented by the following formula (2):

wherein R₁ to R₈, are the same as those in the formula (1), Ar₂ and Ar₄are independently an unsubstituted phenyl group, or a phenyl groupsubstituted with one or more substituents selected from the groupconsisting of an alkyl group, an alkylsilyl group, a cyano group, ahalogen atom, a halogenated alkyl group and a nitro group, R₁₁ to R₂₀are independently a hydrogen atom, an alkyl group, an alkylsilyl group,a cyano group, a halogen atom, a halogenated alkyl group, a nitro groupor a carbonyl group, and at least one of R₁₁ to R₂₀ is a cyano group, afluorine atom, a halogenated alkyl group, a nitro group or a carbonylgroup.
 13. The organic electroluminescence device according to claim 12,wherein Ar₂ and Ar₄ are independently an unsubstituted phenyl group, ora phenyl group substituted with one or more substituents selected fromthe group consisting of an alkyl group, an alkylsilyl group, a cyanogroup and a fluorine atom.
 14. The organic electroluminescence deviceaccording to claim 12, wherein Ar₂ and Ar₄ are independently anunsubstituted phenyl group, or a phenyl group substituted with one ormore substituents selected from the group consisting of a methyl group,an ethyl group, a propyl group, an isopropyl group, a n-butyl group, as-butyl group, an isobutyl group, a t-butyl group, a n-pentyl group, an-hexyl group, alkylsilyl group, a cyano group and a fluorine atom, R₁₁to R₂₀ are independently a hydrogen atom, a methyl group, an ethylgroup, a propyl group, an isopropyl group, a n-butyl group, a s-butylgroup, an isobutyl group, a t-butyl group, a n-pentyl group, a n-hexylgroup, an alkylsilyl group, a cyano group, a fluorine atom, a nitrogroup or a carbonyl group, and at least one of R₁₁ to R₂₀ is a cyanogroup, a fluorine atom, a nitro group or a carbonyl group.
 15. Theorganic electroluminescence device according to claim 12, wherein Ar₂and Ar₄ are independently an unsubstituted phenyl group, or a phenylgroup substituted with one or more substituents selected from the groupconsisting of an alkyl group, an alkylsilyl group, a cyano group, ahalogen atom, a halogenated alkyl group and a nitro group, R₁₁ to R₂₀are independently a hydrogen atom or a cyano group, and at least one ofR₁₁ to R₁₅ is a cyano group, and at least one of R₁₆ to R₂₀ is a cyanogroup.
 16. The organic electroluminescence device according to claim 12,wherein Ar₂ and Ar₄ are independently an unsubstituted phenyl group, ora phenyl group substituted with one or more substituents selected fromthe group consisting of an alkyl group, an alkylsilyl group, a cyanogroup and a fluorine atom, R₁₁ to R₂₀ are independently a hydrogen atomor a cyano group, and at least one of R₁₁ to R₁₅ is a cyano group, andat least one of R₁₆ to R₂₀ is a cyano group.
 17. The organicelectroluminescence device according to claim 12, wherein Ar₂ and Ar₄are independently an unsubstituted phenyl group, or a phenyl groupsubstituted with one or more substituents selected from the groupconsisting of an alkyl group, an alkylsilyl group, a cyano group, ahalogen atom, a halogenated alkyl group and a nitro group, R₁₁, R₁₅, R₁₆and R₂₀ are independently a hydrogen atom or a fluorine atom, R₁₂ to R₁₄and R₁₇ to R₁₉ are a hydrogen atom, and at least one of R₁₁ and R₁₅ is afluorine atom, and at least one of R₁₆ and R₂₀ is a fluorine atom. 18.The organic electroluminescence device according to claim 12, whereinAr₂ and Ar₄ are independently an unsubstituted phenyl group, or a phenylgroup substituted with one or more substituents selected from the groupconsisting of an alkyl group, an alkylsilyl group, a cyano group and afluorine atom, R₁₁, R₁₅, R₁₆ and R₂₀ are independently a hydrogen atomor a fluorine atom, R₁₂ to R₁₄ and R₁₇ to R₁₉ are a hydrogen atom, andat least one of R₁₁ and R₁₅ is a fluorine atom, and at least one of R₁₆and R₂₀ is a fluorine atom.
 19. The organic electroluminescence deviceaccording to claim 4, wherein the alkyl group is a methyl group, anethyl group, a propyl group, an isopropyl group, a n-butyl group, as-butyl group, an isobutyl group, a t-butyl group, a n-pentyl group or an-hexyl group, and the alkylsilyl group is represented by —SiY₃, and Yis independently methyl group, an ethyl group, a propyl group, anisopropyl group, a n-butyl group, a s-butyl group, an isobutyl group, at-butyl group, a n-pentyl group or a n-hexyl group.